(2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol

Base Information

• Chemical Name: (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol
• CAS No.: 315180-76-8
• Molecular Formula: C₂₅H₄₀O₈
• Molecular Weight: 468.588
• Mol file: 315180-76-8.mol

Synonyms:(2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol

Chemical Property of (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol

There total 10 articles about (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(2S,3S,4R)-1-benzyloxy-2,4-bis(2,2-dimethylpropanoyloxymethyl)-3-hydroxy-5-(4-methoxybenzoyloxy)pentane (315180-68-8) → (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol (315180-76-8)

Guidance literature:

With hydrogen; Raney Nickel (W₂); In ethanol; at 20 ℃; for 26h;

DOI:10.1248/cpb.48.1761

Reference yield:

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol (315180-76-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 86 percent / p-TsOH*H₂O / dimethylformamide / 4 h / 55 °C

2.1: 95 percent / n-Bu₃SnH; MgBr₂ / CH₂Cl₂ / 1 h / 20 °C

3.1: 87 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.5 h / -78 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4.2: 83 percent / hexane; tetrahydrofuran / 6 h

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

5.2: 66 percent / aq. KOH; H₂O₂ / tetrahydrofuran / 0.5 h

6.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

7.1: 86 percent / 4 N aq. HCl / tetrahydrofuran / 6 h / 55 °C

8.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

8.2: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

9.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

10.1: 91 percent / H₂ / Raney nickel (W₂) / ethanol / 26 h / 20 °C

With lead(IV) acetate; hydrogenchloride; dmap; n-butyllithium; oxalyl dichloride; hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; magnesium bromide; Raney Nickel (W₂); In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Swern oxidation / 4.2: Wittig methylenation;

DOI:10.1248/cpb.48.1761

Reference yield:

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose (98039-29-3) → (2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-5-(4-methoxybenzoyloxy)pentane-1,3-diol (315180-76-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

1.2: 83 percent / hexane; tetrahydrofuran / 6 h

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

2.2: 66 percent / aq. KOH; H₂O₂ / tetrahydrofuran / 0.5 h

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: 86 percent / 4 N aq. HCl / tetrahydrofuran / 6 h / 55 °C

5.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

5.2: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

6.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

7.1: 91 percent / H₂ / Raney nickel (W₂) / ethanol / 26 h / 20 °C

With lead(IV) acetate; hydrogenchloride; dmap; n-butyllithium; hydrogen; triethylamine; 9-bora-bicyclo[3.3.1]nonane; Raney Nickel (W₂); In tetrahydrofuran; ethanol; hexane; dichloromethane; benzene; 1.2: Wittig methylenation;

DOI:10.1248/cpb.48.1761

upstream raw materials:

(2S,3S,4R)-1-benzyloxy-2,4-bis(2,2-dimethylpropanoyloxymethyl)-3-hydroxy-5-(4-methoxybenzoyloxy)pentane

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzylidene)-α-D-allofuranose

3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Downstream raw materials:

2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester

(2S,3R,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-3,5-[(S)-4-methoxybenzylidenedioxy]pentanal

(2S,3S,4R)-2,4-bis(2,2-dimethylpropanoyloxymethyl)-3,5-[(S)-4-methoxybenzylidenedioxy]pentan-1-ol